CA1273337A - Process for the preparation of 2-amino-6-chloropurine - Google Patents

Process for the preparation of 2-amino-6-chloropurine

Info

Publication number: CA1273337A
Authority: CA; Canada
Prior art keywords: formula; compound; process according; chloride; preparation
Prior art date: 1985-03-23
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

CA000504720A

Other languages

English (en)

French (fr)

Inventor

Michael Raymond Harnden

Richard Lewis Jarvest

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis International Pharmaceutical Ltd

Original Assignee

Beecham Group PLC

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-03-23

Filing date

1986-03-21

Publication date

1990-08-28

1986-03-21 Application filed by Beecham Group PLC filed Critical Beecham Group PLC

1990-08-28 Application granted granted Critical

1990-08-28 Publication of CA1273337A publication Critical patent/CA1273337A/en

2007-08-28 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 18
238000002360 preparation method Methods 0.000 title claims abstract description 9
RYYIULNRIVUMTQ-UHFFFAOYSA-N 6-chloroguanine Chemical compound NC1=NC(Cl)=C2N=CNC2=N1 RYYIULNRIVUMTQ-UHFFFAOYSA-N 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 7
239000012320 chlorinating reagent Substances 0.000 claims abstract description 7
239000003444 phase transfer catalyst Substances 0.000 claims abstract description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical group ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 6
235000019270 ammonium chloride Nutrition 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 2
YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical group [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 claims description 2
125000005210 alkyl ammonium group Chemical group 0.000 claims 2
UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000010992 reflux Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
229940127073 nucleoside analogue Drugs 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000011343 solid material Substances 0.000 description 2
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 2
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
JBMBVWROWJGFMG-UHFFFAOYSA-N 2-chloro-7h-purine Chemical compound ClC1=NC=C2NC=NC2=N1 JBMBVWROWJGFMG-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
239000003443 antiviral agent Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
229940125797 compound 12 Drugs 0.000 description 1
RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
231100000219 mutagenic Toxicity 0.000 description 1
230000003505 mutagenic effect Effects 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
150000003212 purines Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical class N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 description 1
238000002525 ultrasonication Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/40—Heterocyclic compounds containing purine ring systems with halogen atoms or perhalogeno-alkyl radicals directly attached in position 2 or 6

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000504720A 1985-03-23 1986-03-21 Process for the preparation of 2-amino-6-chloropurine Expired - Lifetime CA1273337A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB8507606		1985-03-23
GB858507606A GB8507606D0 (en)	1985-03-23	1985-03-23	Process

Publications (1)

Publication Number	Publication Date
CA1273337A true CA1273337A (en)	1990-08-28

Family

ID=10576527

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000504720A Expired - Lifetime CA1273337A (en)	1985-03-23	1986-03-21	Process for the preparation of 2-amino-6-chloropurine

Country Status (15)

Country	Link
US (1)	US4736029A (pt)
EP (1)	EP0203685B1 (pt)
JP (1)	JPH0670058B2 (pt)
AU (1)	AU589612B2 (pt)
CA (1)	CA1273337A (pt)
DE (1)	DE3681500D1 (pt)
DK (1)	DK165250C (pt)
ES (1)	ES9100017A1 (pt)
GB (1)	GB8507606D0 (pt)
GR (1)	GR860765B (pt)
IE (1)	IE58371B1 (pt)
MX (1)	MX167823B (pt)
NZ (1)	NZ215559A (pt)
PT (1)	PT82245B (pt)
ZA (1)	ZA862129B (pt)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8817270D0 (en) *	1988-07-20	1988-08-24	Beecham Group Plc	Novel process
GB8822236D0 (en) *	1988-09-21	1988-10-26	Beecham Group Plc	Chemical process
GB8918827D0 (en) *	1989-08-17	1989-09-27	Beecham Group Plc	Novel compounds
DE3941657A1 (de) *	1989-12-16	1991-06-20	Hoechst Ag	Verfahren zur herstellung von 2-acylamino-6-halogen-purin aus 2,9-diacylguanin
GB9102127D0 (en) *	1991-01-31	1991-03-13	Smithkline Beecham Plc	Pharmaceuticals
CA2076886C (en) *	1991-11-22	2002-06-11	Masami Igi	Method for production of 2-amino-6-halogenopurine and synthesis intermediate therefor
GB9201961D0 (en)	1992-01-30	1992-03-18	Smithkline Beecham Plc	Pharmaceuticals
DE4231036A1 (de) *	1992-09-17	1994-03-24	Basf Ag	Verfahren zur Herstellung von 2-Amino-6-halogenpurinen
JPH07133276A (ja) *	1993-09-17	1995-05-23	Jiyuuzen Kagaku Kk	２−アセチルアミノ−６−クロロプリンの製造方法
WO1996021664A1 (de) *	1995-01-09	1996-07-18	Lonza Ag	Verfahren zur herstellung von 2-amino-6-chlorpurin und zwischenprodukte dafür
US5789590A (en) *	1995-11-09	1998-08-04	Sumika Fine Chemicals Co., Ltd.	Double cone-like crystal form of 2-amino-6-chloropurine and preparation
CN107629054A (zh) *	2016-07-18	2018-01-26	苏州赛乐生物科技有限公司	一种6‑溴嘌呤的合成方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0141927B1 (en)	1983-08-18	1991-10-30	Beecham Group Plc	Antiviral guanine derivatives

1985
- 1985-03-23 GB GB858507606A patent/GB8507606D0/en active Pending
1986
- 1986-03-20 MX MX009048A patent/MX167823B/es unknown
- 1986-03-21 US US06/844,520 patent/US4736029A/en not_active Expired - Lifetime
- 1986-03-21 EP EP86302105A patent/EP0203685B1/en not_active Expired - Lifetime
- 1986-03-21 PT PT82245A patent/PT82245B/pt unknown
- 1986-03-21 GR GR860765A patent/GR860765B/el unknown
- 1986-03-21 DK DK133586A patent/DK165250C/da not_active IP Right Cessation
- 1986-03-21 CA CA000504720A patent/CA1273337A/en not_active Expired - Lifetime
- 1986-03-21 DE DE8686302105T patent/DE3681500D1/de not_active Expired - Lifetime
- 1986-03-21 ES ES553283A patent/ES9100017A1/es not_active Expired - Fee Related
- 1986-03-21 AU AU55012/86A patent/AU589612B2/en not_active Expired
- 1986-03-21 ZA ZA862129A patent/ZA862129B/xx unknown
- 1986-03-21 NZ NZ215559A patent/NZ215559A/xx unknown
- 1986-03-21 IE IE74186A patent/IE58371B1/en not_active IP Right Cessation
- 1986-03-22 JP JP61064653A patent/JPH0670058B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
ES553283A0 (es)	1991-04-16
PT82245A (en)	1986-04-01
EP0203685B1 (en)	1991-09-18
GB8507606D0 (en)	1985-05-01
DE3681500D1 (de)	1991-10-24
JPS61227583A (ja)	1986-10-09
PT82245B (pt)	1988-02-17
DK165250C (da)	1993-03-22
US4736029A (en)	1988-04-05
DK133586D0 (da)	1986-03-21
DK133586A (da)	1986-09-24
AU5501286A (en)	1986-09-25
NZ215559A (en)	1989-07-27
EP0203685A2 (en)	1986-12-03
IE58371B1 (en)	1993-09-08
ZA862129B (en)	1987-02-25
MX167823B (es)	1993-04-13
EP0203685A3 (en)	1988-06-08
ES9100017A1 (es)	1991-04-16
DK165250B (da)	1992-10-26
AU589612B2 (en)	1989-10-19
IE860741L (en)	1986-09-23
GR860765B (en)	1986-07-21
JPH0670058B2 (ja)	1994-09-07

Legal Events

Date	Code	Title	Description
2007-08-28	MKEX	Expiry

Publication	Publication Date	Title
EP0203685B1 (en)	1991-09-18	Process for the preparation of 2-amino-6-chloro-purine
EP0011399A1 (en)	1980-05-28	N-substituted theophyllines, processes for their preparation and pharmaceutical compositions containing them
KR100213936B1 (ko)	1999-08-02	2-아미노-6-클로로퓨린의 제조방법 및 이를 이용한 펜시클로비르 또는 팜시클로비르의 제조방법
US4767859A (en)	1988-08-30	Process for the preparation of pteridine derivatives
RU2090566C1 (ru)	1997-09-20	Способ получения 9-замещенных производных гуанина
HK1007312B (en)	1999-04-09	Process for the preparation of 2-amino-6-chloropurine and derivatives
EP0483204B1 (en)	1995-05-24	Process for preparing 2,5-diamino-4,6-dichloropyrimidine
AU669874B2 (en)	1996-06-27	Preparation of 2-amino-6-chloropurine
JPS6471846A (en)	1989-03-16	Manufacture of 1,6-di(n3-cyano-n1-guanidino) hexane
FI92400B (fi)	1994-07-29	Natriumpuriinien valmistusmenetelmä
US6455696B2 (en)	2002-09-24	Process for preparing 2,6-dichloropurine
US4959475A (en)	1990-09-25	Process for the production of 2,4-diamino-6-piperidinyl-pyrimidine-3-N-oxide
KR910009957B1 (ko)	1991-12-07	2-푸릴피리미딘 유도체의 제조방법
TSUJI et al.	1978	Syntheses and Reactions of N-Aminothiouracils and Thiadiazolo [3, 2-α] pyrimidinones
JP3064035B2 (ja)	2000-07-12	アミノクロロプリンの製法
CA1330080C (en)	1994-06-07	Process for precipitating cytosine from alkaline solutions with sulphuric acid
CA2145022A1 (en)	1995-09-29	Process for the preparation of 5-formylaminopyrimidines
RU2212406C1 (ru)	2003-09-20	Способ получения 6-замещенных урацилов
Lidak et al.	1970	Synthesis of β-(2-aminopurin-9-yl)-α-alanines
JPH0651682B2 (ja)	1994-07-06	ウラシル誘導体の製造方法